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Issue 16, 2019
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Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

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Abstract

An enantioselective [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones has been successfully developed through a squaramide catalysis strategy. This protocol provides an efficient and mild access to obtain pyrano[2,3-c]pyrrole scaffolds containing contiguous quaternary and tertiary stereogenic centers in excellent yields (up to 99%) with high levels of diastereo- and enantioselectivities (up to 99% ee). Two possible pathways were proposed to explain the observed stereoselectivity.

Graphical abstract: Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

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Publication details

The article was received on 20 Feb 2019, accepted on 26 Mar 2019 and first published on 26 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00419J
Citation: Org. Biomol. Chem., 2019,17, 3945-3950

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    Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones

    Y. Wang, Y. Chen, X. Li, Y. Mao, W. Chen, R. Zhan and H. Huang, Org. Biomol. Chem., 2019, 17, 3945
    DOI: 10.1039/C9OB00419J

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